JP5393170B2 - Electrophotographic photoreceptor - Google Patents

Description

  The present invention relates to an electrophotographic photoreceptor.

  As an electrophotographic photosensitive member used in an image forming apparatus or the like, an electrophotographic photosensitive member having a conductive substrate and a photosensitive layer provided on the conductive substrate is known. The electrophotographic photosensitive member is obtained by applying a coating solution in which a binder resin, a charge generating agent, a charge transporting agent (a hole transporting agent, an electron transporting agent) and the like are dissolved in a solvent, and drying the coating. It is manufactured by forming a photoreceptor layer.

Among the materials used for forming the photoreceptor layer, the electron transfer agent generally tends to have insufficient sensitivity. Therefore, the obtained electrophotographic photoreceptor is difficult to exhibit sufficient photoreceptor characteristics, and the sensitivity is insufficient.
Therefore, in order to solve the problem of the electron transport agent, a quinone derivative is used as an electron transport agent having excellent sensitivity characteristics (Patent Document 1).

  However, even if the quinone derivative described in Patent Document 1 is used as an electron transport agent, it is not always easy to satisfy the sensitivity.

JP 2005-173292 A

  Accordingly, an object of the present invention is to provide an electrophotographic photoreceptor having excellent photoreceptor characteristics and good sensitivity.

  The electrophotographic photoreceptor of the present invention is an electrophotographic photoreceptor having a conductive substrate and a photoreceptor layer provided on the conductive substrate, wherein the photoreceptor layer is represented by the following formulas (1) to (3). It contains the quinone derivative represented by either of these.

In formulas (1) to (3), Ra ¹ , Rb ¹ , Rc ¹ , Ra ² , Rb ² , Rc ² , Ra ³ , Rb ³ , Rc ³ are the same or different and each represents a hydrogen atom, An alkyl group having 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 6 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, Rd ¹ , Rd ² , Rd ³ are the same or different and each represents an alkyl group having 1 to 8 carbon atoms.

  The electrophotographic photoreceptor of the present invention has excellent photoreceptor properties and good sensitivity.

It is a schematic sectional drawing which shows an example of a single layer type electrophotographic photoreceptor. It is a schematic sectional drawing which shows the other example of a single layer type electrophotographic photoreceptor. It is a schematic sectional drawing which shows the other example of a single layer type electrophotographic photoreceptor. 1 is a schematic cross-sectional view showing an example of a laminated electrophotographic photoreceptor. It is a schematic sectional drawing which shows the other example of a laminated type electrophotographic photoreceptor. ^{1 is} a ¹ H-NMR chart of a compound (1-1).

The electrophotographic photoreceptor of the present invention has a conductive substrate and a photoreceptor layer provided on the conductive substrate, and the photoreceptor layer contains a specific quinone derivative.
Examples of the electrophotographic photosensitive member include (i) a single-layer type electrophotographic photosensitive member and (ii) a laminated type electrophotographic photosensitive member, which can be used for either a positive or negative charging type electrophotographic photosensitive member and has a simple structure. (I) single layer for reasons such as easy manufacture, coating film defects at the time of forming a photoreceptor layer can be effectively suppressed, interface between layers is small, and optical characteristics are easily improved. Type electrophotographic photoreceptors are preferred.

(I) Single layer type electrophotographic photosensitive member:
FIG. 1 is a schematic cross-sectional view showing an example of a single layer type electrophotographic photosensitive member. The single layer type electrophotographic photoreceptor 10 includes a conductive substrate 12 and a photoreceptor layer 14 provided on the conductive substrate 12.
The single-layer type electrophotographic photosensitive member 10 is not limited to that shown in FIG. 1, and a single-layer type electrophotographic photosensitive member is interposed between the conductive substrate 12 and the photosensitive layer 14 as shown in FIG. The barrier layer 16 may be provided within a range that does not impede the characteristics of 10, and a protective layer 18 may be provided on the surface of the photoreceptor layer 14 as shown in FIG. 3.

Examples of the conductive substrate include metals such as iron, aluminum, copper, tin, platinum, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, palladium, indium, stainless steel, and brass; Laminated plastic materials; glass coated with aluminum iodide, tin oxide, indium oxide or the like can be used.
Examples of the shape of the conductive substrate include a sheet shape and a drum shape. The shape of the conductive substrate may be appropriately determined according to the structure of the image forming apparatus.

The thickness of the photoreceptor layer is preferably 5 to 100 μm, and more preferably 10 to 50 μm.
The photoreceptor layer is a layer containing a binder resin, a charge generating agent, and a charge transport agent (hole transport agent, electron transport agent).

<Electron transport agent>
In this invention, it contains the quinone derivative represented by either of following formula (1)-(3) as an electron transport agent, It is characterized by the above-mentioned. Hereinafter, the compound represented by Formula (1) is referred to as Compound (1). Other compounds are described in the same manner.

Ra ¹ , Rb ¹ , Rc ¹ , Ra ² , Rb ² , Rc ² , Ra ³ , Rb ³ , Rc ³ are the same or different and each is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or 6 to 12 carbon atoms. An aryl group having 6 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.

Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, t-butyl group, pentyl group, isopentyl group, neopentyl group, and hexyl group.
Examples of the aryl group include a phenyl group, a tolyl group, a xylyl group, a mesityl group, a naphthyl group, a methylnaphthyl group, a benzylphenyl group, a biphenyl group, and an anthranyl group.
Examples of the aralkyl group include a benzyl group, a methylbenzyl group, a phenethyl group, a methylphenethyl group, a phenylbenzyl group, a naphthylmethyl group, and an anthranylmethyl group.
Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, and a cyclodecyl group.
Examples of the alkoxy group include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group and the like.

  These alkyl group, aryl group, aralkyl group, cycloalkyl group and alkoxy group may or may not have a substituent. In particular, when an aryl group, an aralkyl group, a cycloalkyl group, or an alkoxy group has a substituent, the substituent is preferably an alkyl group having 1 to 6 carbon atoms from the viewpoint of improving compatibility with the binder resin. Examples of the alkyl group include the alkyl groups exemplified above.

The ^{Ra 1, Rb 1, Ra 2} , Rb 2, Ra 3, Rb 3, a hydrogen atom, is preferably an alkyl group, particularly a hydrogen atom, a methyl group, t- butyl group.
Rc ¹ , Rc ² , and Rc ³ are preferably hydrogen atoms.

Rd ¹ , Rd ² and Rd ³ are the same or different and are each an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 6 to 12 carbon atoms, or a cycloalkyl having 3 to 10 carbon atoms. Group or an alkoxy group having 1 to 6 carbon atoms.
As an alkyl group, the alkyl group illustrated previously, a heptyl group, an octyl group, etc. are mentioned.
Examples of the aryl group, aralkyl group, cycloalkyl group, and alkoxy group include the aryl group, aralkyl group, cycloalkyl group, and alkoxy group exemplified above.

  These alkyl group, aryl group, aralkyl group, cycloalkyl group and alkoxy group may or may not have a substituent. In particular, when an aryl group, an aralkyl group, a cycloalkyl group, or an alkoxy group has a substituent, the substituent is preferably an alkyl group having 1 to 6 carbon atoms from the viewpoint of improving compatibility with the binder resin. Examples of the alkyl group include the alkyl groups exemplified above.

Rd ¹ , Rd ² , and Rd ³ are preferably alkyl groups, and particularly preferably a methyl group, a pentyl group, and a heptyl group.

  Examples of the compound (1) include compounds (1-1) and (1-2), examples of the compound (2) include compound (2-1), and examples of the compound (3) include compound (3-1). Can be mentioned.

Compound (1) is produced, for example, as follows. In the reaction formula, Ra ^{1 to} Rd ¹ are the same as those in the formula (1).

(A) Process:
In the presence of a catalyst, the compound (41) and the compound (51) are reacted in a solvent to obtain the compound (1), and the compound (1) is extracted and purified.

The reaction ratio (molar ratio) between the compound (41) and the compound (51) is preferably 1: 1 to 1: 2.5. When there is too little compound (41), the yield of compound (1) will decrease. When there are too many compounds (41), there will be many unreacted compounds (41) and it may become difficult to refine | purify a compound (1) by side reaction etc.
The reaction temperature is preferably 50 to 100 ° C., and the reaction time is preferably 2 to 5 hours. By setting it as this range, a desired reaction can be efficiently carried out with a relatively simple production facility.

Examples of the catalyst include ether complexes. Examples of the ether complex include boron trifluoride ether complex. A catalyst may be used individually by 1 type and may be used in combination of 2 or more type.
Examples of the solvent include tetrahydrofuran and dimethylformamide.

Compound (2) was produced in the same manner as Compound (1) except that Compound (42) was used instead of Compound (41) and Compound (52) was used instead of Compound (51) in Step (a). it can. Ra ^{2 to} Rd ² are the same as in the description of the formula (2).

Compound (3) was produced in the same manner as Compound (1) except that Compound (43) was used instead of Compound (41) and Compound (53) was used instead of Compound (51) in Step (a). it can. Ra ^{3 to} Rd ³ are the same as in the description of the formula (3).

  Since the compounds (1) to (3) described above have a highly lipophilic substituent, they are excellent in compatibility with the binder resin. Therefore, the compounds (1) to (3) have high sensitivity as electron transport agents for electrophotographic photoreceptors.

In the present invention, any of compound (1) to compound (3) is used as the electron transport agent, but other electron transport agents may be used in combination.
Examples of the electron transfer agent include quinone derivatives, excluding compounds (1) to (3), anthraquinone derivatives, malononitrile derivatives, thiopyran derivatives, trinitrothioxanthone derivatives, 3,4,5,7-tetranitro-9-fluorenone derivatives, dinitro. Anthracene derivative, dinitroacridine derivative, nitroantharaquinone derivative, dinitroanthraquinone derivative, tetracyanoethylene, 2,4,8-trinitrothioxanthone, dinitrobenzene, dinitroanthracene, dinitroacridine, nitroanthraquinone, dinitroanthraquinone, succinic anhydride, Examples thereof include maleic anhydride and dibromomaleic anhydride. These electron transfer agents may be used alone or in combination of two or more.

<Hole transport agent>
Examples of the hole transport agent include enamine compounds, oxadiazole compounds such as 2,5-di (4-methylaminophenyl) -1,3,4-oxadiazole, and 9- (4-diethylaminostyryl) anthracene. Styryl compounds such as polyvinylcarbazole, organic polysilane compounds, pyrazoline compounds such as 1-phenyl-3- (p-dimethylaminophenyl) pyrazoline, hydrazone compounds, indole compounds, oxazole compounds, Examples thereof include nitrogen-containing cyclic compounds such as isoxazole compounds, thiazole compounds, thiadiazole compounds, imidazole compounds, pyrazole compounds, and triazole compounds, and condensed polycyclic compounds. These hole transport agents may be used alone or in combination of two or more.
As the hole transport agent, the compound (6-1) is particularly preferable.

<Charge generator>
Examples of the charge generator include phthalocyanine pigments, perylene pigments, bisazo pigments, diketopyrrolopyrrole pigments, metal-free naphthalocyanine pigments, metal naphthalocyanine pigments, squaraine pigments, trisazo pigments, indigo pigments, azurenium pigments, cyanine pigments, Organic photoconductors such as pyrylium pigment, ansanthrone pigment, triphenylmethane pigment, selenium pigment, toluidine pigment, pyrazoline pigment, quinacridone pigment; selenium, selenium-tellurium, selenium-arsenic, cadmium sulfide, amorphous silicon, etc. And inorganic photoconductive agents. A charge generating agent may be used individually by 1 type, and may be used in combination of 2 or more type.

  As the charge generating agent, an electrophotographic photosensitive member having more excellent sensitivity characteristics, electrical characteristics, stability, and the like can be obtained. Therefore, metal-free phthalocyanine (τ type or X type), titanyl phthalocyanine (α type or Y type), One or more selected from the group consisting of hydroxygallium phthalocyanine (type V) and chlorogallium phthalocyanine (type II) is preferred.

<Binder resin>
Examples of the binder resin include polycarbonate resins such as bisphenol Z type, bisphenol Z type, bisphenol C type, and bisphenol A type, polyarylate resin, styrene-butadiene copolymer, styrene-acrylonitrile copolymer, styrene-maleic acid. Copolymer, acrylic copolymer, styrene-acrylic acid copolymer, polyethylene resin, ethylene-vinyl acetate copolymer, chlorinated polyethylene resin, polyvinyl chloride resin, polypropylene resin, ionomer resin, vinyl chloride-vinyl acetate copolymer Polymers, alkyd resins, polyamide resins, polyurethane resins, polysulfone resins, diallyl phthalate resins, ketone resins, polyvinyl butyral resins, polyether resins, etc .; silicone resins, epoxy resins, phenol resins, Containing resins, thermosetting resins such as melamine resin, epoxy acrylate, urethane - photocurable resins such as acrylate. Binder resin may be used individually by 1 type, and may be used in combination of 2 or more type.

The photoreceptor layer may contain a known additive as long as the electrophotographic characteristics are not adversely affected. Examples of additives include antioxidants, radical scavengers, singlet quenchers, deterioration inhibitors such as ultraviolet absorbers, softeners, plasticizers, surface modifiers, extenders, thickeners, dispersion stabilizers. , Wax, acceptor, donor and the like.
In order to improve the sensitivity of the photoreceptor layer, known sensitizers such as terphenyl, halonaphthoquinones, and acenaphthylene may be used in combination with the charge generator.

5-100 mass parts is preferable with respect to 100 mass parts of binder resin, and, as for content of an electron transport agent, 10-80 mass parts is more preferable.
20-500 mass parts is preferable with respect to 100 mass parts of binder resin, and, as for content of a hole transport agent, 30-200 mass parts is more preferable.
The content of the charge generating agent is preferably 0.1 to 50 parts by mass, and more preferably 0.5 to 30 parts by mass with respect to 100 parts by mass of the binder resin.

The photoreceptor layer is formed, for example, by applying a coating solution in which an electron transport agent, a hole transport agent, a charge generator, and a binder resin are dissolved or dispersed in a solvent on a conductive substrate and drying. The
The coating liquid is prepared by dissolving or dispersing each component in a solvent using a roll mill, a ball mill, an attritor, a paint shaker, an ultrasonic disperser or the like. As a coating method, a known method may be used.

Examples of the solvent include alcohols such as methanol, ethanol, isopropanol and butanol; aliphatic hydrocarbons such as n-hexane, octane and cyclohexane; aromatic hydrocarbons such as benzene, toluene and xylene; dichloromethane, dichloroethane, Halogenated hydrocarbons such as chloroform, carbon tetrachloride and chlorobenzene; ethers such as dimethyl ether, diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether and diethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone and cyclohexanone; esters such as ethyl acetate and methyl acetate Dimethylformaldehyde, dimethylformamide, dimethyl sulfoxide and the like. A solvent may be used individually by 1 type and may be used in mixture of 2 or more types.
In order to improve the dispersibility of each component and the smoothness of the surface of the photoreceptor layer, a surfactant, a leveling agent, and the like may be added to the coating solution.

  Since the obtained single layer type electrophotographic photoreceptor has a photoreceptor layer containing a specific quinone derivative (compound (1) to compound (3)), it has excellent photoreceptor characteristics and good sensitivity.

(Ii) Multilayer electrophotographic photoreceptor:
FIG. 4 is a schematic cross-sectional view showing an example of a laminated electrophotographic photosensitive member. The multilayer electrophotographic photoreceptor 20 includes a conductive substrate 12, a charge generation layer 24 containing a charge generation agent provided on the conductive substrate 12, and a charge transport layer 22 provided on the charge generation layer 24. And have. In the multilayer electrophotographic photoreceptor 20, the charge generation layer 24 and the charge transport layer 22 constitute a photoreceptor layer.

The multilayer electrophotographic photosensitive member 20 is not limited to that shown in FIG. 4, and as shown in FIG. 5, a charge transport layer 22 is provided on the conductive substrate 12, and charge generation is generated on the charge transport layer 22. A layer 24 may be provided. However, since the charge generation layer 24 is thinner than the charge transport layer 22, the charge transport layer 22 is preferably provided on the charge generation layer 24 in order to protect the charge generation layer 24.
Examples of the conductive substrate include those similar to the single-layer type electrophotographic photosensitive member.

The thickness of the charge generation layer is preferably from 0.01 to 5 μm, and more preferably from 0.1 to 3 μm.
The thickness of the charge transport layer is preferably 2 to 100 μm, and more preferably 5 to 50 μm.
Depending on the order of formation of the charge generation layer and the charge transport layer, and the type of charge transport agent used in the charge transport layer, the laminate type electrophotographic photoreceptor is selected as a positive or negative charge type.

Examples of the electron transport agent, the hole transport agent, the charge generating agent, and the binder include the same materials as in the single-layer type electrophotographic photosensitive member.
The content of the charge generation agent in the charge generation layer is preferably 5 to 1000 parts by mass, more preferably 30 to 500 parts by mass with respect to 100 parts by mass of the binder resin.
When the hole transport agent is contained in the charge generation layer, the content of the hole transport agent is preferably 10 to 500 parts by weight, and more preferably 50 to 200 parts by weight with respect to 100 parts by weight of the binder resin.

The content of the electron transport agent in the charge transport layer is preferably 5 to 200 parts by weight, more preferably 10 to 100 parts by weight with respect to 100 parts by weight of the binder resin.
10-500 mass parts is preferable with respect to 100 mass parts of binder resin, and, as for content of the hole transport agent of a charge transport layer, 25-200 mass parts is more preferable.

The charge generation layer is formed, for example, by means such as vapor deposition or coating.
The charge transport layer is formed by means such as coating as in the case of the photoreceptor layer of a single-layer electrophotographic photoreceptor.

  Since the obtained multilayer electrophotographic photoreceptor has a photoreceptor layer containing a specific quinone derivative (compound (1) to compound (3)), it has excellent photoreceptor properties and good sensitivity.

Each evaluation in the examples was performed as follows.
(Electrical characteristics test)
The single layer type electrophotographic photosensitive member was installed in a drum sensitivity tester manufactured by GENTEC, and the single layer type electrophotographic photosensitive member was charged so that the initial surface potential was + 700V. Next, monochromatic light (light intensity 1.5 μJ / cm ² ) having a wavelength of 780 nm (half-value width 20 nm) extracted from the white light of the halogen lamp using a bandpass filter is applied to the surface of the single-layer electrophotographic photosensitive member. The surface potential was measured after 0.5 second from the start of exposure and measured as the residual potential (V). Note that the lower the residual potential, the higher the sensitivity.

[Production of Compound (1-1)]
(A) Process:
In a 200 mL flask, 2.2 g (10 mmol) of the compound (41-1) and 2.19 g (10 mmol) of the compound (51-1) were placed, and after argon gas replacement, 100 mL of dry THF was added and dissolved. Then, a catalytic amount of boron trifluoride etherate was added and stirred for 5 hours while heating at 80 ° C. After cooling to room temperature, the reaction solution was poured into ion exchange water, extracted with chloroform, and the organic layer (reaction solution) was washed 5 times with ion exchange water. Subsequently, after the solvent in the organic layer was distilled off, the residue was purified by column chromatography (developing solvent: chloroform / hexane = 1/1) to obtain 3.37 g of a solid compound (1-1). (Yield 80%).

¹ H-NMR (300 MHz) was measured for the compound (1-1). As a solvent, CDCl ₃ was used, and TMS was used as a reference substance. It was confirmed that compound (1-1) was obtained. ^{The 1} H-NMR chart is shown in FIG.

<Example 1>
5 parts by mass of an X-type metal-free phthalocyanine as a charge generating agent, 50 parts by mass of a compound (1-1) as an electron transport agent, 80 parts by mass of a compound (6-1) as a hole transport agent, and a binder resin 100 parts by mass of a certain polycarbonate resin was mixed and dispersed in 800 parts by mass of tetrahydrofuran as a solvent with a ball mill for 50 hours to prepare a coating solution for a single-layer type photoreceptor layer. Next, this coating solution is applied on a conductive substrate made of an aluminum base tube by a dip coating method and dried with hot air at 100 ° C. for 30 minutes to form a photosensitive layer having a thickness of 30 μm. A photoreceptor was obtained. The single layer type electrophotographic photosensitive member was subjected to an electrical property test. The results are shown in Table 1.

<Example 2>
A single-layer electrophotographic photosensitive member was produced and evaluated in the same manner as in Example 1 except that Y-type titanyl phthalocyanine was used instead of X-type metal-free phthalocyanine as the charge generating agent. The results are shown in Table 1.

[Production of Compound (1-2)]
2.53 g of compound (1-2) was obtained in the same manner as compound (1-1) except that 1.35 g (10 mmol) of compound (51-2) was used instead of compound (51-1). (Yield 75%).

<Example 3>
A single-layer electrophotographic photosensitive member was produced and evaluated in the same manner as in Example 1 except that the compound (1-2) was used instead of the compound (1-1) as the electron transfer agent. The results are shown in Table 1.

<Example 4>
Example 1 except that compound (1-2) was used instead of compound (1-1) as the electron transport agent and Y type titanyl phthalocyanine was used as the charge generating agent instead of X type metal-free phthalocyanine. Similarly, a single layer type electrophotographic photosensitive member was produced and evaluated. The results are shown in Table 1.

[Production of Compound ( 2-1 )]
Instead of the compound (41-1), 1.72 g (10 mmol) of the compound (42-1) was used, and instead of the compound (51-1), 1.91 g (10 mmol) of the compound (52-1) was used. Except for the above, 1.73 g of compound ( 2-1 ) was obtained in the same manner as compound (1-1) (yield 50%).

<Example 5>
A single-layer electrophotographic photosensitive member was produced and evaluated in the same manner as in Example 1 except that the compound ( 2-1 ) was used instead of the compound (1-1) as the electron transfer agent. The results are shown in Table 1.

<Example 6>
Example 1 except that compound ( 2-1 ) was used instead of compound (1-1) as the electron transport agent, and Y type titanyl phthalocyanine was used as the charge generating agent instead of X type metal-free phthalocyanine. Similarly, a single layer type electrophotographic photosensitive member was produced and evaluated. The results are shown in Table 1.

[Production of Compound ( 3-1 )]
Compound ( 3-1 ) 3.02g was obtained like compound (1-1) except having used compound (43-1) 2.64g (10mmol) instead of compound (41-1). (Yield 65%).

<Example 7>
A single-layer electrophotographic photosensitive member was produced and evaluated in the same manner as in Example 1 except that the compound ( 3-1 ) was used instead of the compound (1-1) as the electron transfer agent. The results are shown in Table 1.

<Example 8>
Example 1 except that compound ( 3-1 ) was used instead of compound (1-1) as the electron transport agent and Y type titanyl phthalocyanine was used as the charge generating agent instead of X type metal-free phthalocyanine. Similarly, a single layer type electrophotographic photosensitive member was produced and evaluated. The results are shown in Table 1.

[Compound (7-1)]
<Comparative Example 1>
A single-layer electrophotographic photosensitive member was produced and evaluated in the same manner as in Example 1 except that the compound (7-1) shown below was used instead of the compound (1-1) as the electron transporting agent. The results are shown in Table 1.

<Comparative example 2>
Example 1 except that compound (7-1) was used instead of compound (1-1) as the electron transport agent and Y type titanyl phthalocyanine was used as the charge generating agent instead of X type metal-free phthalocyanine. Similarly, a single layer type electrophotographic photosensitive member was produced and evaluated. The results are shown in Table 1.

[Production of Compound (7-2)]
1.85 g of compound (7-2) was obtained in the same manner as compound (1-1) except that 1.07 g (10 mmol) of compound (51-3) was used instead of compound (51-1). (Yield 60%).

<Comparative Example 3>
A single-layer electrophotographic photosensitive member was produced and evaluated in the same manner as in Example 1 except that the compound (7-2) was used instead of the compound (1-1) as the electron transport agent. The results are shown in Table 1.

<Comparative Example 4>
Example 1 except that compound (7-2) was used instead of compound (1-1) as the electron transport agent and Y type titanyl phthalocyanine was used as the charge generating agent instead of X type metal-free phthalocyanine. Similarly, a single layer type electrophotographic photosensitive member was produced and evaluated. The results are shown in Table 1.

[Production of Compound (7-3)]
Instead of compound (51-1), 2.44 g of compound (7-3) was obtained in the same manner as compound (1-1) except that 1.23 g (10 mmol) of compound (51-4) was used. (Yield 75%).

<Comparative Example 5>
A single-layer electrophotographic photosensitive member was produced and evaluated in the same manner as in Example 1 except that the compound (7-3) was used instead of the compound (1-1) as the electron transport agent. The results are shown in Table 1.

<Comparative Example 6>
Example 1 except that compound (7-3) was used instead of compound (1-1) as the electron transport agent, and Y type titanyl phthalocyanine was used as the charge generating agent instead of X type metal-free phthalocyanine. Similarly, a single layer type electrophotographic photosensitive member was produced and evaluated. The results are shown in Table 1.

[Production of Compound (7-4)]
In place of the compound (41-1), 1.72 g (10 mmol) of the compound (42-1) was used, and 1.21 g (10 mmol) of the compound (52-2) was used in place of the compound (51-1). Otherwise, 1.79 g of compound (7-4) was obtained in the same manner as compound (1-1) (yield 65%).

<Comparative Example 7>
A single-layer electrophotographic photosensitive member was produced and evaluated in the same manner as in Example 1 except that the compound (7-4) was used instead of the compound (1-1) as the electron transport agent. The results are shown in Table 1.

<Comparative Example 8>
Example 1 except that compound (7-4) was used instead of compound (1-1) as the electron transport agent and Y type titanyl phthalocyanine was used as the charge generating agent instead of X type metal-free phthalocyanine. Similarly, a single layer type electrophotographic photosensitive member was produced and evaluated. The results are shown in Table 1.

[Production of Compound (7-5)]
Instead of the compound (41-1), 2.64 g (10 mmol) of the compound (43-1) was used, and 1.07 g (10 mmol) of the compound (51-3) was used instead of the compound (51-1). Except for the above, in the same manner as in the compound (1-1), 1.94 g of the compound (7-5) was obtained (yield 55%).

<Comparative Example 9>
A single-layer electrophotographic photosensitive member was produced and evaluated in the same manner as in Example 1 except that the compound (7-5) was used instead of the compound (1-1) as the electron transfer agent. The results are shown in Table 1.

<Comparative Example 10>
Example 1 except that compound (7-5) was used instead of compound (1-1) as the electron transport agent and Y type titanyl phthalocyanine was used as the charge generating agent instead of X type metal-free phthalocyanine. Similarly, a single layer type electrophotographic photosensitive member was produced and evaluated. The results are shown in Table 1.

As is apparent from Table 1, the single layer type electrophotographic photosensitive member of the example had a lower residual potential than the single layer type electrophotographic photosensitive member of the comparative example.
On the other hand, the single layer type electrophotographic photoreceptor of the comparative example had a high residual potential.
In the single layer type electrophotographic photosensitive member obtained in Comparative Examples 9 and 10, the electron transport agent crystallized and deposited on the surface of the photosensitive member when the coating liquid for the single layer type photosensitive layer was applied. The residual potential could not be measured. Therefore, the evaluation test was not performed.

  Since the electrophotographic photoreceptor of the present invention contains a specific quinone derivative excellent in compatibility with the binder resin in the photoreceptor layer, the photoreceptor characteristics are excellent and the sensitivity is good. The electrophotographic photosensitive member is expected to contribute to high speed and high performance of various image forming apparatuses.

  DESCRIPTION OF SYMBOLS 10 Single layer type electrophotographic photosensitive member (electrophotographic photosensitive member) 12 Conductive substrate 14 Photosensitive member layer 20 Laminated electrophotographic photosensitive member (electrophotographic photosensitive member) 22 Charge transport layer (photosensitive member layer) 24 Charge generating layer (photosensitive member) Body layer)

Claims (1)

In an electrophotographic photoreceptor having a conductive substrate and a photoreceptor layer provided on the conductive substrate,
An electrophotographic photoreceptor, wherein the photoreceptor layer contains a quinone derivative represented by any of the following formulas (1) to (3).

In formulas (1) to (3), Ra ¹ , Rb ¹ , Rc ¹ , Ra ² , Rb ² , Rc ² , Ra ³ , Rb ³ , Rc ³ are the same or different and each represents a hydrogen atom, An alkyl group having 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 6 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, Rd ¹ , Rd ² , Rd ³ are the same or different and each represents an alkyl group having 1 to 8 carbon atoms.

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